Electric Literature of 626248-56-4, A common heterocyclic compound, 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, molecular formula is C8H8N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To 130 mg (0.37 mmol) of 2, 118 mg of the 3-(2H-l,2,3-triazol-2-yl)aniline (1.2 eq), 107 mg NaCvBu (3 eq), 85 mg Pd(dba)2 (0.4 eq), and 53 mg Q-Phos (Aldrich 675784, 0.2 eq) was added ~5 mL dry toluene. The reaction mixture was degassed with Ar for 10 min and then refluxed under argon at 110C for 3 hours. The reaction mixture was cooled and diluted with EtOAc, washed with water and brine, dried over MgSC^, and concentrated. The resulting oil was dissolved in a 3: 1 mixture of TFA/H2S04. The mixture was heated to 80C for 1 hour and then cooled to room temperature. Approximately 10 mL H20 was added to the mixture and the resulting solution was subjected to reverse phase preparative HPLC. Product was isolated by utilizing a mobile phase with 0.1% TFA in water as solvent A and 0.1% TFA in acetonitrile as solvent B and eluting with a 15% to 50% B mixture over 10 minutes.[0527] Yield: 23 mg. UV: 265, 306 nm. M+H found for C^H^NsO: 393.3. NMR(CD3OD): 8.96 (IH, br), 7.96 (2H, s), 7.82 (IH, d, J=8.8Hz), 7.67 (IH, d, J=6.0Hz), 7.42 (IH, t, J=6.0Hz), 7.17 (IH, d, J=5.6Hz), 6.18 (IH, d, J=8.8Hz), 4.78 (IH, br), 3.65 (IH, br), 1.90-1.45 (8H, m) ppm.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics